What It’s Like To Date While Grieving

Spoiler alert: It’s f*cking hard.

Erin Mosbaugh

Feb 23, 2019 | 5:00 PM

Photo by Javier Díez/Stocksy

Dating, as I see it, is the attempt to find a person who complements you, supports you, and makes you feel like you’re home. Grief, on the other hand, is an ocean you swim through, an ocean in which every stretch of water has a different weight and temperature. At times the water is warm and buoyant; other times it is cold and so heavy you think you will drown.

Both experiences require a ton of emotional energy and self-reflection, and when you combine them — well, it can be intense. It can also be hilarious, horrifying, and just straight-up uncomfortable to date after you’ve lost a family member or someone you loved.

A few months before my mom died, I met a whiskey-drinking, Massachusetts-bred, salt-of-the-earth freelance camera guy who loved going to trivia night with his bros. He was new to Los Angeles, my hometown, and didn’t have all that much of his life together. But we had fun and he seemed sensitive (for a male), and I was hopeful. Plus, he kind of looked like a dad, and I had lost mine a few years back.

Just four months after we had the “Will you be my girlfriend?” conversation, he and my best friend Julia laid with me on the floor at Cedars Sinai Intensive Care Unit and held me after I watched my mom slip into the unknown.

I leaned into him hard those next few months, and he became the solid body next to me I could grab and cry into. We moved into a one-bedroom apartment together because I didn’t feel like going back to my apartment alone. At the time I felt claustrophobic and suffocated in my own body. I felt like the ocean was pulling me under. Unsurprisingly, I also felt suffocated sharing a 700-square-foot apartment with my partner.

My grief was big, and it was very raw. I was feeling particularly agitated and angry about my mother’s death one afternoon, and I told him I was going to go running. I felt suffocated and unstable. The endorphins only served to make me angrier, and I came back and slammed a shot of tequila. It was 2 p.m.

“If you’ve lost someone in your intimate relational pool, like a parent or a sibling, then your stability and balance has been rocked in your area of your self identity,” explains Kate Cummins, Psy.D. “You’re not going to be able to be the most stable, self-actualized version of yourself when you’re going out and dating people and figuring out whether or not you’re going to be a good match for them,” Cummins adds.

As much as I love tequila and welcome an afternoon margarita with friends, this was for sure not the most stable version of me. There were times I felt like giving up, but I didn’t. I took the train to work, and occasionally went to yoga, got old fashioneds with friends, shopped at Whole Foods 365, cooked, and traveled. Was I operating at 40-percent capacity? You bet I was. But I was doing everything in my power to keep going.

Eight months into living with my boyfriend, he broke it off. “I’m exhausted, and I don’t know what I’m doing in this relationship, let alone in Los Angeles,” he said. It’s pretty rare that a new relationship can bear a crisis, according to my therapist and to my own life experience. My now-ex and I were both depleted.

I kept meeting people, too, but dating was drastically different. I had been through the worst, and anything that could go wrong on a date was nothing compared to what I had overcome.

“When you go through a life crisis, a lot of people reevaluate what they value and what they want out of life,” says Cummins. “For example, if you are in a relationship that’s dysfunctional, you will likely end it because you want to work on yourself and your self-identity.”

I moved out and into my own apartment that was spacious, sunny, and beautiful, and my family friends decorated it so it felt like a home. I hung a postcard that said, “Learn the art of solitude. Get to know yourself” and another that said “We get to make ourselves and we get to make our family” on my fridge.

Those first few months in that apartment, I felt a specific type of aloneness I had never before in my life experienced — I felt I had no safety net, no backup, no one watching over me. But I didn’t let fear of the aloneness stop me. I didn’t stop going to work, I didn’t stop traveling, I didn’t stop dating casually and having sex, and I didn’t stop reaching out to friends for help.

“It’s so much easier to focus on a relationship with someone else than to focus on your own stuff,” explains Cummins. “Not many people can sit in silence with themselves. Not many people can date themselves. But the greatest challenge, the greatest thing to do when you have lost someone, is to really date yourself, take yourself out, and to get to know and understand yourself so that you can move into the next chapter.”

A few months after the breakup, I started to really sit with myself and pay attention to what I was feeling and what I needed. I got a beautiful dog, a couple meaningful tattoos, and let myself sit on the couch for hours and stare out the window. I kept meeting people, too, but dating was drastically different. I had been through the worst, and anything that could go wrong on a date was nothing compared to what I had overcome.

A year or so after my mom died, I met up with a man I connected with on Tinder. When he asked me, “Where do your parents live?” I promptly blurted out, “My parents are both dead!” That’s when he told me both of his parents had also passed away. (My sister-in-law was quick to ask, “Are you sure you’re not on a dating app for adult orphans?” She‘s a morbid one, but witty as hell.)

I continued seeing the guy because he could relate to me on a level few others could — but ultimately, he was not right for me, and besides, I was still very much dating myself.

I went on to date a married couple who became my good friends as well as sexual partners. I dated a guy who talked to me about his techniques for lucid dreaming and his strategies for mindfulness. And then I met a woman, and this one felt different.

She recently lost a parent figure, and like with my mother, it was unexpected. She has the soul of someone who understands pain but also wants to create beauty. She is ambitious, thoughtful, and analytical — plus she loves drinking coffee on the couch, going to therapy, Korean restaurants, and talking about attachment theory and psychology just as much as I do.

I ask myself what my parents would think of her (they’d love her), of me dating women (they’d be down with it), and of me writing an article about dating while grieving their deaths.

I can’t ask them directly, but I can talk to them out loud, feel their presence, and talk with the people I’m dating about my parents’ quirks, talents, and mannerisms.

Not everyone wants to hear about my dad overnighting pulled pork burritos from his kitchen in LA to my office in New York. And not everyone wants to hear about how my mom worked at group homes in Downey with abused teenage girls. But the right person — when he or she comes along — will want to know all of it. Every last pulled pork burrito story there is to tell. And while I realize it’s only the beginning of our relationship, the woman I’m dating now is that person.

Meanwhile, my approach to dating (and to life) has been altered drastically. I’ve been through the worst, so how bad could a breakup — or anything really — be? How bad could weird stares at a party be when people realize I’m holding hands with another woman?

There’s a freedom in not giving a fuck that is indescribable, and not giving a fuck has led me to what feels like the person I could spend the rest of my life with.